Water → HCID 10977719, compound

HRID 1281867Notes

Reaction equation

HRID 1281867 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1Br)=[O:11].[C:18](=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:18][C:15]1[S:14][C:13]2[O:1][C:2]3[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=3[NH:9][C:10](=[O:11])[C:12]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18422293HCID 18422293, compound

Product 1

HCID 10977719HCID 10977719, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of N-(2-hydroxy-4-methylphenyl)-2-bromo-3-thiophenecarboxamide (3.4 g) in dimethyl sulfoxide (30 ml) was added potassium carbonate (2.9 g) and the mixture was stirred at 140-150° C. for 1 hour. The reaction system was cooled to room temperature and the reaction mixture was poured into water. The precipitated crystals were collected by filtration, washed with water and purified by silica gel column chromatography (chloroform) to give 2, 8-dimethylthieno[2,3-b][1,5]benzoxazepin-4(5H)-one (1.2 g).

Workup

  1. temperatureThe reaction system was cooled to room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water
  4. custompurified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-1808532a93b047a88dcab9e3f8cc6358
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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